Hydrazine → Isoquinoline-3-carbohydrazide

HRID 340886

Reaction equation

HRID 340886 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O:13]C)=O)[N:2]=1.[NH2:15][NH2:16]>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([NH:15][NH2:16])=[O:13])[N:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 725374Methyl 3-isoquinolinecarboxylate

Product 1

HCID 55263898Isoquinoline-3-carbohydrazideYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl isoquinoline-3-carboxylate (10 g, 53.42 mmol) in ethanol (100 mL) was added hydrazine (17.1 g). The reaction mixture was refluxed for 30 min and concentrated under high vacuum to remove hydrazine. The resulting residue was triturated with ethanol (20 mL) to give isoquinoline-3-carbohydrazide (8.6 g, 86%). LRMS (M+H+) m/z 188.1.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. concentrationconcentrated under high vacuum
  3. customto remove hydrazine
  4. customThe resulting residue was triturated with ethanol (20 mL)

Sources & evidence

ORD record
ord-326e316ddfb74c1f8b140e81d1113f34
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Linked notes

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